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Description: Gemcitabine hydrochloride (formerly also known as LY-188011, NSC 613327; dFdC; dFdCyd; gemcitabine; trade name: Gemzar), an antimetabolite anticancer drug, is a potent DNA synthesis inhibitor with IC50 of 50 nM, 40 nM, 18 nM and 12 nM in PANC1, MIAPaCa2, BxPC3 and Capan2 cells, respectively. Gemcitabine is converted intracellularly to the active metabolites difluorodeoxycytidine di- and triphosphate (dFdCDP, dFdCTP). dFdCDP inhibits ribonucleotide reductase, thereby decreasing the deoxynucleotide pool available for DNA synthesis.
References: Oncology. 2002;62(4):354-62; J Gastrointest Surg. 2012 Jul;16(7):1333-40.
Related CAS#:95058-81-4 (free base); 210829-30-4 [Gemcitabine elaidate, also known as CO-101 and CP-4126, is a lipophilic, unsaturated fatty acid ester derivative of gemcitabine (dFdC)]; 116371-67-6 (Gemcitabine monophosphate free acid); 1638288-31-9 (Gemcitabine monophosphate disodium salt); 840506-29-8 [Acelarin (NUC-1031) is a ProTide transformation and enhancement of the widely-used nucleoside analogue, gemcitabine]; 892128-60-8 (LY2334737, an orally bioavailable prodrug of gemcitabine)
Abbreviations: dFdC; dFdCyd; LY188011; LY-188011; LY 188011; gemcitabine; Gemzar.
Chemical Name: 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one hydrochloride
SMILES Code: O=C1N=C(N)C=CN1[[email protected]@H]2O[[email protected]](CO)[[email protected]@H](O)C2(F)F.[H]Cl
Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
This equation is commonly abbreviated as: C1V1 = C2V2
In vitro activity: Gemcitabine induced NF-κB activity in BxPC-3, PANC-1, and MIA PaCa-2 cells and decreased the level of the NF-κB inhibitor IκBα in BxPC-3 and PANC-1 cells. Treatment of BxPC-3 cells with low dose Gemcitabine for 48 hours results in a dose-dependent increase in NF-κB binding. In contrast, NF-κB DNA binding is decreased in BxPC-3 cells treated with the higher Gemcitabine doses for 48 h; however, 24-h treatment with these higher doses increases NF-κB binding in BxPC-3 cells.
Cell Assay: BxPC-3, MIA PaCa-2, and PANC-1 cells are seeded in a 96-well plate. After 24 hours, cells are treated with vehicle, DMAPT and/or Gemcitabine for an additional 24 hours or 48 hours. Apoptosis is quantified using the Cell Death Detection ELISA to detect the amount of cytoplasmic histone-associated DNA fragments and expressed relative to vehicle-treated cells.
Purity ≥98%
COA
MSDS
NMR